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A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

ABSTRACT: An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (R)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. These chiral allyl alcohols are prepared for food analysis and screening insect attractants.

SUBMITTER: Liu J

PROVIDER: S-EPMC6155351 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

Liu Jia J Li Honglian H Zheng Chao C Lu Shichao S Guo Xianru X Yin Xinming X Na Risong R Yu Bin B Yu Bin B Wang Min M

Molecules (Basel, Switzerland) 20170227 3

An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (<i>R</i>)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. ...[more]

PMID: 28264452

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